Hosts: Caitlin Ferguson (COOPilots.io) and Rob Ripp (Fintelligent, Author of Finance for Founders)
are a COO-CFO duo discussing supporting founders through growth challenges.

This episode covers:

Spotting Bandwidth Bottlenecks

• Obvious signs: Missed deadlines, quality issues, constant firefighting
• Subtle "energy leaks": Team disengagement, people stepping back, energy drops
• Catch energy issues before they impact client deliverables

Hiring Economics: Fractional vs. Full-Time

• Before hiring, check: Cash flow positive? Stable pipeline? Profit margin and runway?
• The math: If fractionals billing halftime at 3x hourly rate, full-time likely costs less
• Utilization targets: 75-80% for junior staff, max 85% (accounting for PTO)
• Bring in-house when: Core client-facing roles, IP development, culture representation needed
• Keep 1099 when: Behind-scenes work, specific deliverables, works independently

Cash Management Essentials

• Burn rate formula: (Cost of Revenue + Operating Expenses) ÷ 6 months = monthly burn
• Get line of credit at founding (best time to borrow: when you don't need it)
• Set your "squeal point" - how many months before making changes
• Without accountability, easy to think you're "one month away" indefinitely

Letting Go of Wrong People

• Case study: Employee with good delivery but high resistance, taking 10 hours/week of founder time
• Key question: "If those 10 hours could generate $1M in sales, is keeping them worth it?"
• Why founders struggle: Loyalty to early supporters, family/friends, falling in love with potential vs. outcomes
• The cost: Resentment builds, relationships damaged irreparably
• Solution: Present trade-offs clearly, let them opt in/out of new direction

Metrics & Accountability

• Define success upfront with clear measures
• Microsoft Education Competencies: Framework defining beginner to advanced performance by skill
• Pick 5 organizational + 3-5 role-specific competencies
• Professional services: 60% how people experience work, 40% outcomes

Building the Right Number Two

• Founder roles: Develop business, develop talent. That's it.
• COO role: Trains run on time, ensures delivery, has tough conversations with founder
• Must be truly empowered - no undermining their decisions
• Find complement to your strengths, not clone
• Long-term: COO often becomes CEO for premium exit

The Emotional Journey

• Founders operate in vacuums, need advisors who understand risk-taking
• Mastermind communities and experienced fractionals provide benchmarks
• No founder with great exit did it alone

Assessment Tools

• FinSight (Fintelligent): Financial data + recommendations, ~2 weeks
• VIP Audit (COO Pilots): Values/vision + team interviews + 30-60-90 plan, ~2 weeks, podcast listener rate

Notable Quotes

• Caitlin: "Energy leaks - you can see it as much in the output as in your people."
• Caitlin: "Founders confuse 'I'm busy' with 'I can afford someone.'"
• Caitlin: "If those 10 hours could generate a million dollar sale, would keeping this person be worth it?"
• Rob: "Founders have two roles: develop new business, develop talent. COO: trains run on time."

Resources Mentioned:

• FinSight Tool (Fintelligent) - Financial assessment
• Altitude 90™ Audit (COO Pilots) - Org health check and 30/60/90 roadmap to relieve pressure - Mention the podcast for $1,000 off
• Microsoft Education Competencies - Performance framework, example of Dealing with Ambiguity

Hosts: Caitlin Ferguson (COOPilots.io) and Rob Ripp (Fintelligent, Author of Finance for Founders)
are a COO-CFO duo discussing supporting founders through growth challenges.

This episode covers:

The CFO-COO Partnership

• Finance and operations are highly aligned in founder support work
• Issues often start in one area (messy books) and reveal needs in the other (operational improvements)
• Both hosts have served 200+ founders collectively, generating significant value ($20M+ for Caitlin's clients, $200-300M+ in exit value for Rob's clients)

Common Founder Challenges ("New Level, New Devil")

• Heroic effort syndrome: Working 60-80 hour weeks leading to burnout
• Fear of delegation: Either wrong people in seats or mental barriers to letting go
• Infrastructure issues: From brittle systems to shiny object syndrome
• Decision paralysis: Getting stuck at the whiteboard with too many options

Building Trust with Founders

• Communication through process: Keeping founders informed via notifications and regular updates
• Active listening: Asking open-ended questions rather than prescriptive solutions
• Understanding founder values: Aligning processes and team selection with core motivations
• Transparency: "Candor with kindness and challenging with intent"

The Scaling Challenge

• Founders must transition from "grit alone" to strategic delegation
• 80-90% execution by others is better than 100% founder execution at unsustainable hours
• A-players need empowerment to do their jobs effectively
• "Seagull management" (swooping in uninvited) kills team motivation

Key Metrics and Outcomes

• For Operations: Improved utilization rates, higher margins, better client retention
• For Finance: Clean books, clear metrics, path to exit valuation
• Rule of 40: Combination of growth rate and EBITDA percentage
• Valuation focus: EBITDA multiples and enterprise value optimization

Notable Quotes

• Caitlin: "You won't scale if you don't [delegate]. There's no path to being a scale by being a superhero."
• Rob: "100% of founders say 'I wish I'd done this sooner' after letting go and getting help."
• Caitlin: "New level, new devil" - each growth stage brings new challenges

Client Engagement Process

Both hosts emphasize:

• Audit-first approach: Understanding current state before recommending changes
• Custom 30-60-90 day plans: Tailored to specific business needs and opportunities
• Team interviews: Getting 360-degree feedback to build buy-in
• Quick wins: Demonstrating value within 30 days or less

This podcast is produced by Could Be Pretty Cool, an Atlanta-based media company amplifying creative voices through storytelling, strategy, and sound.

Coming September & October 2025

In this kickoff, Caitlin Ferguson (Founder of COOPilots.io) and Rob Ripp (Founder of Fintelligent & author of Finance for Founders) set the stage for a podcast built for founders who are scaling beyond grit alone.

You’ll hear what brought us together, why we’re passionate about guiding founders through the messy middle, and what to expect in upcoming episodes. Think real stories (names changed) from the trenches and practical tips you can use right away.

This isn’t another dry business lecture. We want you to feel like you're sitting down with two trusted peers over coffee. We’ll cover:

• How finance and operations fuel growth (and exits)

• Common mistakes founders make between $1M–$10M in revenue

• What “clean numbers” and “repeatable systems” really look like

• Why scaling without the stress is not only possible, but essential

If you’ve ever thought: “We’re growing, but I still feel stuck in the weeds" then this podcast is for you.

Subscribe here for updates and notifications when new episodes are released.